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Cas Database |
| Name |
2(3H)-Furanone,dihydro-5-methyl-, (5R)- |
EINECS | N/A |
| CAS No. | 58917-25-2 | Density | 1.04 g/cm3 |
| PSA | 26.30000 | LogP | 0.71190 |
| Solubility | N/A | Melting Point |
N/A |
| Formula | C5H8O2 | Boiling Point | 206.6 °C at 760 mmHg |
| Molecular Weight | 100.117 | Flash Point | 75 °C |
| Transport Information | N/A | Appearance | N/A |
| Safety | 26-36 | Risk Codes | 22-36-36/37/38 |
| Molecular Structure |
|
Hazard Symbols |
 Xi, Xn
|
| Synonyms |
2(3H)-Furanone,dihydro-5-methyl-, (R)-;(+)-4-Methylbutyrolactone;(+)-g-Methylbutyrolactone;(+)-g-Pentalactone;(+)-g-Valerolactone;(5R)-5-Methyldihydrofuran-2(3H)-one;(5R)-Dihydro-5-methyl-2(3H)-furanone;(R)-(+)-g-Valerolactone;(R)-4-Methylbutyrolactone;(R)-4-Pentanolide;(R)-5-Methyldihydrofuran-2(3H)-one;(R)-5-Methyldihydrofuran-2-one;(R)-g-Pentalactone;(R)-g-Valerolactone; |
Article Data | 59 |
2(3H)-Furanone,dihydro-5-methyl-, (5R)- Synthetic route
- 624-45-3
levulinic acid methyl ester
- 58917-25-2
(R)-5-methyl-2-oxotetrahydrofuran
| Conditions | Yield |
|---|---|
| With hydrogenchloride; hydrogen; [RuCl2-((R)-binap)]*NEt3 In methanol at 40℃; under 2068.6 Torr; for 48h; | 99% |
| With hydrogenchloride; ruthenium trichloride; hydrogen; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl In methanol at 60℃; under 45603.1 Torr; for 10h; Autoclave; optical yield given as %ee; | 88% |
| Stage #1: levulinic acid methyl ester With hydrogen In methanol at 65℃; under 68255.5 Torr; for 48h; Stage #2: With sulfuric acid In methanol Heating; | 72% |
| With Rhodococcus ruber alcohol dehydrogenase; isopropyl alcohol In aq. buffer at 30℃; for 24h; pH=9; Enzymatic reaction; | n/a |
- 1219498-05-1
(S)-2-[(R)-4-hydroxypentanamide]-3-phenyl-N-[(R)-1-phenylethyl]propanamide
A
- 58917-25-2
(R)-5-methyl-2-oxotetrahydrofuran
B
- 133287-30-6
(S)-2-amino-3-phenyl-N-[(R)-1-phenylethyl]propanamide
| Conditions | Yield |
|---|---|
| With hydrogenchloride In methanol for 3h; Reflux; | A 93% B 96% |
- 99631-16-0
ethyl (S)-4-hydroxypentanoate
- 58917-25-2
(R)-5-methyl-2-oxotetrahydrofuran
| Conditions | Yield |
|---|---|
| With toluene-4-sulfonic acid In methanol at 20℃; for 20h; Inert atmosphere; enantioselective reaction; | 92% |
- 155847-13-5
γ-hydroxyvaleric acid
- 58917-25-2
(R)-5-methyl-2-oxotetrahydrofuran
| Conditions | Yield |
|---|---|
| With hydrogenchloride In water at 20℃; enantioselective reaction; | 91% |
| With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 6h; | 83% |
| With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 6h; | 83% |
| With hydrogenchloride at 25℃; for 16h; Yield given; |
- 58917-25-2
(R)-5-methyl-2-oxotetrahydrofuran
| Conditions | Yield |
|---|---|
| With toluene-4-sulfonic acid In methanol at 20℃; for 24h; | 87% |
- 85428-31-5
3-(S)-oxiranyl-propionic acid methyl ester
- 58917-25-2
(R)-5-methyl-2-oxotetrahydrofuran
| Conditions | Yield |
|---|---|
| With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; sodium iodide In 1,2-dimethoxyethane for 2h; Heating; | 85% |
- 58879-34-8
(S)-5-tosyloxypentan-4-olide
- 58917-25-2
(R)-5-methyl-2-oxotetrahydrofuran
| Conditions | Yield |
|---|---|
| With tri-n-butyl-tin hydride; sodium iodide; 2,2'-azobis(isobutyronitrile) | 79% |
| Multi-step reaction with 2 steps 1: 74 percent / LAH / tetrahydrofuran / 3 h / Heating 2: 40 percent / Ag2CO3/Celite / CHCl3 / 12 h / Heating View Scheme |
- 75351-36-9
(R)-3-hydroxy-1-(p-toluenesulfonyloxy)butane
- 58917-25-2
(R)-5-methyl-2-oxotetrahydrofuran
| Conditions | Yield |
|---|---|
| Stage #1: potassium cyanide; (R)-3-hydroxy-1-(p-toluenesulfonyloxy)butane In ethanol; water for 16h; Reflux; Stage #2: With hydrogenchloride In ethanol; water for 24h; Reflux; | 75% |
- 151-50-8
potassium cyanide
- 75351-36-9
(R)-3-hydroxy-1-(p-toluenesulfonyloxy)butane
- 58917-25-2
(R)-5-methyl-2-oxotetrahydrofuran
| Conditions | Yield |
|---|---|
| With hydrogenchloride In ethanol; water 1.) reflux, 16 h, 2.) reflux, 24 h; | 68% |
- 123-76-2
levulinic acid
- 58917-25-2
(R)-5-methyl-2-oxotetrahydrofuran
| Conditions | Yield |
|---|---|
| With yeast Pichia farinosa in a glucose medium at 30℃; for 48h; | 67% |
| Multi-step reaction with 2 steps 1: 83 percent / (-)-diisopinocampheylborane / tetrahydrofuran / 17 h / 20 °C 2: 83 percent / CF3CO2H / CH2Cl2 / 6 h / 0 - 20 °C View Scheme | |
| Multi-step reaction with 2 steps 1: C67H80IrNOP(1+)*C32H12BF24(1-); hydrogen; triethylamine / methanol / 24 h / 65 °C 2: hydrogenchloride / water / 20 °C View Scheme |
2(3H)-Furanone,dihydro-5-methyl-, (5R)- Specification
This chemical is called 2(3H)-Furanone,dihydro-5-methyl-, (5R)-, and its systematic name is (5R)-5-methyldihydrofuran-2(3H)-one. With the molecular formula of C5H8O2, its molecular weight is 100.12. The CAS registry number of this chemical is 58917-25-2. Additionally, its product categories are Chiral Compounds; Lactones; Chiral.
Other characteristics of the 2(3H)-Furanone,dihydro-5-methyl-, (5R)- can be summarised as followings: (1)ACD/LogP: -0.27; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.27; (4)ACD/LogD (pH 7.4): -0.27; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 16.94; (8)ACD/KOC (pH 7.4): 16.94; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.43; (14)Molar Refractivity: 24.89 cm3; (15)Molar Volume: 96.2 cm3; (16)Polarizability: 9.86×10-24cm3; (17)Surface Tension: 29.3 dyne/cm; (18)Density: 1.04 g/cm3; (19)Flash Point: 75 °C; (20)Enthalpy of Vaporization: 44.29 kJ/mol; (21)Boiling Point: 206.6 °C at 760 mmHg; (22)Vapour Pressure: 0.235 mmHg at 25°C.
Production method of this chemical: The 2(3H)-Furanone,dihydro-5-methyl-, (5R)- could be obtained by the reactant of 4-oxo-pentanoic acid methyl ester. This reaction needs the reagent of H2, conc. aq. HCl, the solvent of methanol and the catalyst of *NEt3. The yield is 99 %. In addition, this reaction should be taken for 48 hours at the temperature of 40 °C. The other condition is the pressure of 2068.6.
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When you are using this chemical, please be cautious about it as the following: This chemical is irritating to eyes, respiratory system and skin. You should wear suitable protective clothing when you use it. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
1.SMILES: O=C1O[C@H](C)CC1
2.InChI: InChI=1/C5H8O2/c1-4-2-3-5(6)7-4/h4H,2-3H2,1H3/t4-/m1/s1
3.InChIKey: GAEKPEKOJKCEMS-SCSAIBSYBT
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